Pyridine → 2-(4-Methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarboxamide

HRID 584729Notes

Reaction equation

HRID 584729 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.C(OCC)(=O)C.O1CCCC1>C1(C)C=CC=CC=1.O>[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:10][C:11]([NH2:13])=[O:12])=[O:27])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 3419712-(4-Methoxyphenyl)hydrazinecarboxamideHCID 21939870Tetrahydrofuran ethyl acetate

Product 1

HCID 223415812-(4-Methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarboxamideYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a suspension of 2-(4-methoxyphenyl)hydrazinecarboxamide (1.81 g, 9.99 mmol) in 20 mL of toluene, pyridine (1.01 mL, 12.5 mmol) and then a solution of 4-methoxybenzoyl chloride (2.13 g, 12.5 mmol) in 10 mL of toluene were added. The mixture was refluxed with stirring for 1 hour. After cooling, 500 mL of ethyl acetate-tetrahydrofuran (9:1) and 100 mL of water were added to the mixture. After vigorous shaking, an insoluble material was isolated by filtration and dired in vacuo to give 2-(4-methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarboxamide (1.95 g, 61.9% yield).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureAfter cooling
  3. customAfter vigorous shaking, an insoluble material was isolated by filtration and dired in vacuo

Sources & evidence

ORD record
ord-edbe269e48cb4d83b9b53cf0ecce9ca8
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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